Max raeck



Patented Oct. 29,1929

UNITED STATES PATENTOFFICE MAX RAECK, OF DESSAU-ZIEBIGK, GERMANY, ASSIGNOR TO I. G. FARBENINDO STRIE AKTIENGESIELSCHAFT, OF FRANKFORT-ON-THE-MAIN, GERMANY, A CORPORATION OF GERMANY PROCESS OF PRODUCING DERIVATIVES OF 2-HYDROXYNAPHTHALENE-S-CARIBOXYLIC ACID AMIDE No Drawing. Application filed Hatch 20, 1828; Serial No. 283,224, and in. Germany April 22, 1927.

By the present invention derivatives of 2- hydroxynaphthalene-3-carboxylic acid amide, which are of high importance in the dyeing art, are made by heating 2-hydroxynaph- '5 thalene-3-carhoxy1ic acid witha mustard oil.

The reaction occurs in a surprlslngly smooth manner and with very good ield.

For example, 18.8 parts y weight of 2- hydroxyna hthalene-3-carboxylic acid are heated wit 13.5 parts by welght of phenyl mustard oil at about 220 C. until evolution of carbon oxysulfide is at an end. On cooling,

the 2-hydroxynaphtha1ene-3-carboxylic acid phenylamide crystallizes in a very pure form.

The yield is quantitative. The reaction may be explained by the equation:

H on I I v O I. w 0 +sG-o coon s -o-N c 0-NH Iiisteadof phenyl mustard 'oil any ester of,

isothiocyanio acid can be used with like resuit, for instance an alkyl mustard oil or an aryl mustard oil, substituted or not in the nucleus, such as a tolyl mustard oil, a chlorophenyl mustard oil, or a naphthyl mustard 011. y What I claim is:

1. Process of producingQ-hydroxynaphthalene-B-carboxylic acid amides by treating 2-hydroxynaphthalene-3-carboxylicacidwith a mustard oil. 2. Process of producing Q-hydroxynaphtha1ene-3-carboxylic acid amides by treating 2-hydroxynaphthalene-3-carb0xy1ic acid with an ar 1 mustard oil.

3. rocess of producing Q-hydroxynaphthalene-3 -carboxylic acid 'phenylamide by heating 2-hydroxynaphthalene-3-carboxylic acid with phenyl mustard oil.

In testimony whereof I aflix my signature.

MAX RAECK. 

